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Zum Verhalten von Olefinen, konjugierten Dienen und Steroidolefinen gegenüber Pb(OCOCF3)4

Reactions of Pb(OCOCF3)4 with olefines, conjugated dienes and steroid olefines

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The reaction of Pb(OCOCF3)4 with several olefines and conjugated dienes is reported. The oxidation of styrene, stilbene and 1.4-dihydro-1.4-methanonaphthalene leads to phenylacetaldehyde (1), benzaldehyde (2) and benzophenone (3), and to,9R+2R,9S)-diol-bis-trifluoroacetate (8) respectively. Of the conjugated dienes, 1.3-cyclohexadiene yieldscis-2-cyclohexene-1.4-diol bis-trifluoroacetate (4), cyclopentadiene yieldscis-2-cyclopentene-1.4-diolbis-trifluoroacetate (5) andtrans-2-cyclopentene-1.4-diol-bis-trifluoroacetate (6) andE,E-2.4-hexadiene yields the isomers of 3-hexene-2.5-diol bis trifluoroacetate (7). Oxidation of unsaturated steroids such as 2-cholestene, 2-androsten-17-one, 4-cholestene, androsta-4.9(11)-diene-3.17-dione and 3β-acetoxy-5-cholestene results in cholestane-2α,3α-diol diacetate (9), 2α,3α-diacetoxyandrostan-17-one (10) and 1α-acetoxy-2-androsten-17-one (11), in coprostane-4β,5β-diol-4β-trifluoroacetate (12) or coprostane 4β,5β-diol-4β-acetate (12a), 4-cholestanone (13), in 12α-trifluoroacetoxyandrosta-4,9(11)-diene-3.17-dione (14), and in cholestane-3β,5α,6α-triol-3β-acetate-6α-trifluoracetate.

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  1. 1

    R. E. Partch, J. Amer. Chem. Soc.89, 3662 (1967).

  2. 2

    J. R. Campbell, J. R. Kalman, J. T. Pinhey undS. Sternhell, Tetrahedron Lett.18, 1763 (1972).

  3. 3

    J. R. Kalman, J. T. Pinhey undS. Sternhell, Tetrahedron Lett.52, 5369 (1972).

  4. 4

    D. Westphal undE. Zbiral, im Druck.

  5. 5

    F. Huber undM. S. A. El-Meligy, Z. anorg. allg. Chem.399 349 (1973).

  6. 6

    K. B. Wiberg, Oxidation in Organic Chemistry, Vol. 5-A. New York-London: Acad. Press, und hieraus angeführte Referenzen.

  7. 7

    G. E. Heasley, V. L. Heasley, S. L. Manatt, H. A. Day, R. V. Hodges, P. A. Kroon, D. A. Redfield, T. L. Rold undD. E. Williamson, J. Org. Chem.38, 4109 (1973).

  8. 8a

    K. Alder, F. Flock undH. Wirtz, Chem. Ber.91, 609 (1958).

  9. 8b

    J. Meinwald undG. A. Wiley, J. Amer. Chem. Soc.80, 3667 (1958).

  10. 9

    H. B. Henbest undM. Smith, J. Chem. Soc. [London]1957, 926.

  11. 10a

    J. F. Eastham, G. B. Miles undC. H. Krauth, J. Amer. Chem. Soc.81, 3114 (1959).

  12. 10b

    D. Lavie, Y. Kashman undE. Glotter, Tetrahedron22, 1103 (1966).

  13. 11

    D. H. R. Barton undW. J. Rosenfelder, J. Chem. Soc.1951, 1048.

  14. 12

    E. Zbiral undH. Hugl, Tetrahedron29, 769 (1973).

  15. 13

    V. Schwarz undS. Hermanek, Collect. Czech. Chem. Commun.29, 2360 (1964).

  16. 14

    V. Prelog undE. Tagmann, Helv. chim. Acta27, 1867 (1944).

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Correspondence to Prof. Dr. Erich Zbiral.

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Westphal, D., Zbiral, E. Zum Verhalten von Olefinen, konjugierten Dienen und Steroidolefinen gegenüber Pb(OCOCF3)4 . Monatshefte für Chemie 106, 679–693 (1975).

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